104206-82-8 Usage
Description
Mesotrione (2-[4-(methylsulfonyl)-2-nitrobenzoyl]-cylohexane-1,3-dione) is a selective herbicide which is also referred to as Callisto and Tenacity (trademarks). It was introduced to the market in 2001 for use in maize plantations as a control measure against grass and broad-leaved weeds. Mesotrione is a triketone herbicide which was formulated after the discovery of the naturally occurring phytotoxin leptospermone secreted by the Callistemon citrinus plant.
Chemical and Physical Properties
Mesotrione is a light yellow opaque solid with a faint pleasant odour. It dissolves at a rate of 2.2 g/l at 200 C in unbuffered water whose pH is 4.8. It also dissolves in n-heptane <0.5, xylene 1.6, toluene 3.1, methanol 4.6, ethyl acetate 18.6, 1,2-dichloroethane 66.3, acetone 93.3, and in acetonitrile 117.0, all in g/l at 200 C.
Mesotrione has a molecular weight of 339.318 g/mol, a monoisotopic mass of 339.041 g/mol and an exact mass of 339.041 g/mol. It has a heavy atom count of 23 and a complexity of 627.
Mechanism of Action
Studies indicate that the toxic influence of the compound can be attributed to high plasma concentration levels of tyrosine which is resultant of inhibition by 4-hydroxyphenylpyruvate dioxygenase (HPPD). HPPD is an essential constituent of the biochemical route that aids the conversion of tyrosine to alpha-tocopherol and plastoquino\ne.
Mesotrione is a highly potent agonist of HPPD against Arabidopsis thaliana, which is indicated by the Ki figure of c 6-18 pM. It is readily absorbed by weed species after foliar application and it is widely distributed to various parts of the plant through basipetal and acropetal movement.
Maize crops are generally tolerant to Mesotrione as a result of selective metabolism by the plant. The compound may take a relatively long time to be absorbed in some weed species hence Mesotrione is applied as a selective herbicide in maize plantations.
The plasma half-life of the compound is approximately 1 hour.
Preparation
Mesotrione is synthesized through the reaction of acetyl chloride with 3-methylmercaptonitrobenzene with aluminum trichloride as the catalyst. The relative ketone is oxidized with sodium oxychloride which results in the 4-methylsulfonyl compound, which is condensed with cyclohexane-1,3-dione to obtain the respective enol ester. The latter is reorganized to the appropriate form of the product with potassium cyanide with triethylamine as the catalyst.?
Mesotrione is available as a soluble solid or concentrates, as a pressurized liquid, a ready to use solution, soluble concentrate, emulsifiable concentrate, water dispersible granules and in granular form.?
Some of its premix partners may include terbuthylazine, Rimsulfron, Nicosulfron, S-Metolachlor, Glyphosphate and Atrazine.
Consumption
A study indicated that the total usage of the compound in the last 5 years is primarily in corn, which accounts for about 98% of the total acres treated and the total pounds of the applied Mesotrione. Field corn accounts for the highest percentage of the treated crops in regards to the acres treated and the acreage of crops grown at 20.2%.
Precautionary Statements
The applicator should put on protective gear when handling Mesotrione concentrate or contaminated surfaces. It is recommended that one avoids eating, drinking or smoking while handling the product and that one should always wash off any splashes that come into contact with the skin immediately.?
During the application process, the sprayer should ensure that the machine is calibrated appropriately, the nozzles are in a matched set and the machine is adjusted to the respective level of the crop. The concentrates should not be left in the sprayer for extended periods of time.?
Mesotrione may cause mild or acute eye irritation. However, it is not a dermal irritant.
Uses
Different sources of media describe the Uses of 104206-82-8 differently. You can refer to the following data:
1. Mesotrione is a herbicide that works by inhibiting 4-hydroxyphenylpyruvate dioxygenase (HPPD), a crucial enzyme for the biosynthesis of carotenoid in plants. Mesotrione is also a synthetic analog of l
epospermone.
2. Herbicide.
Definition
ChEBI: An aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group.
Check Digit Verification of cas no
The CAS Registry Mumber 104206-82-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,2,0 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 104206-82:
(8*1)+(7*0)+(6*4)+(5*2)+(4*0)+(3*6)+(2*8)+(1*2)=78
78 % 10 = 8
So 104206-82-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H13NO7S/c1-23(21,22)8-5-6-9(10(7-8)15(19)20)14(18)13-11(16)3-2-4-12(13)17/h5-7,13H,2-4H2,1H3
104206-82-8Relevant articles and documents
Preparation method of mesotrione
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Paragraph 0046; 0060; 0061-0082, (2021/08/11)
The invention provides a preparation method of mesotrione. The preparation method comprises: S1) carrying out a reaction on 2-nitro-4-methylsulfonylbenzoyl chloride and 1, 3-cyclohexanedione in the presence of an acid-binding agent to obtain an enol ester reaction liquid; and S2) adding a rearrangement agent as shown in a formula (I) into the enol ester reaction liquid, and performing a rearrangement reaction to obtain mesotrione. Compared with the prior art, the method has the advantages that the rearrangement agent containing unsaturated double bonds is adopted, under the synergistic effect of the double bonds, the rearrangement agent has better reactivity and reaction rate in the rearrangement reaction process, and the green and environment-friendly aftertreatment method is simple.
Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
supporting information, p. 433 - 438 (2020/02/13)
The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
Synthetic process of methyl sulcotrione
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Paragraph 0016; 0017; 0018; 0019; 0020; 0021, (2019/06/11)
The invention discloses a synthetic process of methyl sulcotrione. 2-nitro-4-methylsulfony benzoic acid and 1,3-cyclohexanedione are added into a solvent, then, a catalyst and an addition agent are added, temperature is raised to 140-150 DEG C under stirring, and condensation reaction is directly carried out; and then, rearrangement is carried out to obtain the methyl sulcotrione. According to thesynthetic process of the methyl sulcotrione, the catalyst and the addition agent are added for dehydration, so that the condensation reaction is directly carried out on the 2-nitro-4-methylsulfony benzoic acid and the 1,3-cyclohexanedione; and then, the rearrangement is carried out to obtain a methyl sulcotrione product. Due to no adding of thionyl chloride or phosgene for chlorination, reactionsteps are reduced, and meanwhile, tail gas treatment or production safety is further avoided; and in addition, acid-binding agents are not added, and later wastewater treatment is reduced. Therefore,used raw materials are less, and greenness, environmental protection and no pollution are achieved.
